How the OSS Shaped the CIA and American Special Ops

Wild Bill Donovan’s admirers and critics still argue over his legacy, but on one point they agree: His World War II Office of Strategic Service (OSS) became the Petri dish for the spies who later ran the CIA as well as the special operators who conduct some of the most daring raids the world has ever seen.  Picture of Will Bill Donovan is at right.


Four CIA directors — Allen Dulles, Richard Helms, William Colby and William Casey — learned the craft of clandestine warfare as operatives for Donovan’s OSS. Indeed, the daring, the risk-taking, the unconventional thinking, and the élan and esprit de corps of the OSS permeated the new agency.

So would the OSS’s failings: the delusions that covert operations, like magic bullets, could produce spectacular results, or that legal or ethical corners could be cut for a higher cause. Dulles launched the calamitous operation to land CIA-trained, anti-Castro guerrillas at Cuba’s Bay of Pigs. Helms was convicted of lying to Congress about the CIA’s effort to oust President Salvador Allende in Chile. Colby would become a pariah among the agency’s old hands for releasing to Congress what became known as the “Family Jewels” report on CIA misdeeds during the 1950s, ‘60s, and early ‘70s. Casey would nearly bring down the CIA — and Ronald Reagan’s presidency — from the scheme to secretly supply Nicaragua’s Contras with money raked off from the sale of arms to Iran in exchange for American hostages in Beirut.

Few appreciate how remarkable it was that President Franklin Roosevelt appointed William J. “Wild Bill” Donovan, in July 1941, to be the head of an intelligence organization called the Coordinator of Information, later renamed the Office of Strategic Services. Donovan was a Republican, Roosevelt was a Democrat, and the two had a history of fierce political battles in New York. But to Roosevelt, Donovan — a hero of the Great War and part of the Republican Party’s internationalist wing — was the only one who seemed to be thinking seriously about how to set up a worldwide foreign intelligence service, which FDR desperately needed as the cyclone of World War II approached the United States.

Donovan started with just one man — himself. By the end of the war, he had been promoted to major general and had assembled a force of more than 10,000 spies, saboteurs, commandos, propagandists, research analysts, and support personnel operating in stations all over the world. He had clandestine officers who stole secrets from the Axis, guerrillas who fought behind enemy lines, some of the country’s finest minds analyzing the intelligence, and psychological warfare specialists who tried to sap enemy morale.

Based in Switzerland, Dulles ran the OSS’s most successful spy operation against the Third Reich. Casey organized dangerous missions to penetrate Nazi Germany. Colby led daring commando raids into occupied France and Norway. Helms mounted risky intelligence programs against the Russians in war-torn Berlin just after the German surrender.

After FDR died, President Harry Truman, who was not close to Donovan and had received derogatory reports on the OSS and its director, shut down the agency on October 1, 1945, and parceled out its functions to the Pentagon and State Department. Truman was not blind to the need for a foreign intelligence service to spy on future Cold War threats. He just didn’t want Donovan and his OSS leading it. In 1947, however, Truman created the Central Intelligence Agency, whose organization practically mirrored the postwar spy service Donovan had in mind and was staffed by a number of OSS alumni.

Dulles ran the CIA as he had his OSS station in Switzerland. He believed that intelligence was a key part of American foreign policy and that the network of associations, the breadth of vision and the daring he had displayed fighting the Nazis would succeed in battling communism. Spying during the war and afterwards was a gentleman’s pursuit, he believed, practiced in the shadows by and among “men of affairs” like him, who were comfortable bending ethics or cutting legal corners for a higher cause. Though he talked little about Donovan after the war, Dulles’s operating style mirrored the general’s in many ways. Like Donovan, Dulles showed no interest in managing the CIA’s inner workings, leaving them to his deputies so he could be free to dabble in the clandestine operations that interested him.

Helms, who took over the CIA in 1966, had no vision for recasting the agency as Dulles had. His strength, as it had been in postwar Berlin, was management, not innovation. He was also determined to keep the CIA out of the headlines, ordering division heads to scrub covert operations overseas for security and shut down the ones in danger of being exposed. Though Helms was a demanding taskmaster, subordinates groused that he was too soft on the “old boys club” of former OSS officers in the agency, which needed shaking up. Helms wanted to keep his distance from old World War II spy pals so he wouldn’t be seen as playing favorites as director, but play favorites he did. He pulled OSS officers’ children who had joined the CIA out of meetings to give them a special welcome in his seventh-floor office at Langley. He often balked at firing veterans who misbehaved overseas, instead finding out-of-the-way jobs for them in headquarters.

Colby, who liked to putter around his Bethesda, Maryland home wearing his floppy Army fatigue cap from World War II, was profoundly affected by his OSS experience, say friends and relatives. As Director of Central Intelligence he drove his own car to work, ate with employees in the cafeteria, called in young analysts to compliment them on their reports and suggest ways their work could be improved, and found time in his schedule to listen to any employee walking in with a complaint. Like Donovan, he believed the mundane work of information gathering often produced more valuable intelligence than a Mata Hari-style escapade. With advances in electronic intelligence gathering, the human spy was a “contributor, but not the sole actor,” he said.

Casey hung two photos on the wall of his seventh-floor office — portraits of Ronald Reagan and Wild Bill Donovan. He ran the CIA the way he thought the general would. Like Donovan, he kept his door open to all ideas for operations. He hated bureaucracy, circumvented the chain of command, and poked his head into offices rungs below. He was proud, as Donovan had been, of the vast array of PhDs working at Langley. Like Donovan, he loved to tour his overseas stations, not only to boost morale and size up field officers who worked for him but also to leave Washington’s political wars behind. When he returned, he always delivered vivid trip reports to President Reagan, just as Donovan had done with Roosevelt.

Today, a statue of Donovan, commissioned by Casey when he was Director of Central Intelligence, stands in the main foyer of the CIA’s headquarters building — a symbolic reminder that Donovan was the father of modern American espionage. The basic skills agency officers practice today differ little from those of their OSS predecessors, save for more modern technology.

The U.S. Special Operations Command (USSOCOM) also claims an OSS lineage. Donovan’s special operations teams, for example, supplied partisans with weapons to fight the Nazis in Yugoslavia. His Detachment 101 organized guerrilla attacks against Japanese military targets in Burma. The OSS also fielded more than a thousand highly trained, foreign language-speaking paratroopers, skilled in sabotage and small-arms tactics, who were used in small groups to harass the enemy. These Operational Group commandos, called OG’s, fought behind the lines in France and Italy. A glass-enclosed case, full of Donovan memorabilia, sits in the main foyer of USSOCOM’s Tampa, Florida headquarters. The command’s leaders have held brainstorming sessions to explore what this modern force can learn from its roots and how it can emulate the special operations fighters of the OSS.

Donovan can also be considered the father of the psychological operations USSOCOM and the CIA wage. In the OSS, these were called morale operations and the technology used was, in some cases, far cruder than the kind used in today’s dark arts. Donovan’s officers planted rumors in newspapers claiming that top Nazis were abandoning Germans and fleeing to South America, dropped leaflets on Wehrmacht soldiers, and beamed radio broadcasts at them with propaganda messages mixed with songs by Marlene Dietrich.

Clearly, Donovan was one of the men who shaped modern unconventional warfare. Today’s shadow warriors who practice espionage, launch covert attacks, or try to change hearts and minds overseas can trace their heritage back to the OSS and its band of “glorious amateurs.”

Article by Douglas Waller from War on The Rocks



Douglas Waller is an author, lecturer, and former correspondent for Time magazine. He is the author of Disciples: The World War II Missions of the CIA Directors Who Fought for Wild Bill Donovan (Simon & Schuster) which will be released on October 6. He also wrote Wild Bill Donovan: The Spymaster Who Created the OSS and Modern American Espionage (2011), described by Booklist as “the definitive biography of a seminal figure in the history of American intelligence.”

The Pentagon's Secret Warrior Retires

Here's to a former Green Beret and Quiet Professional. The Pentagon's Secret Warrior leaves the Pentagon as Quietly as he entered. Asked what he is looking forward to, Michael G. Vickers, who retired this week as under secretary of defense for intelligence, answered without hesitation: “Sleeping.”

Having participated in virtually every significant global crisis of the past four decades, either as a supporting player or just as often cast in a starring, if un-credited, role, he has missed a lot of that. “I get kept awake by near-term things and long-term things,” he says.

Most Americans do not even know the job Mr. Vickers is leaving, just days after his 62nd birthday, even though the Pentagon commands the intelligence community’s largest share of the vast federal budget for spying, about $80 billion, and manages the most intelligence employees, about 180,000 people.

For a man who once practiced infiltrating Soviet lines with a backpack-size nuclear weapon, Mr. Vickers has a mellow, professorial demeanor. In addition to Army Special Forces training, he has studied Spanish, Czech and Russian and holds a doctorate in strategy from Johns Hopkins University. (Of his 1,000-page dissertation, he says, “It’s a good doorstop.”) His answers to policy questions are disciplined, cautious and usually organized in two parts, or three, or more.

So ask: What exactly kept you awake? First, as the military would say, are the crocodiles closest to the canoe.

“Our immediate threats are terrorism, particularly from global jihadist groups that want to attack the United States. It is a constant danger,” Mr. Vickers said. “And cyber is now in that category.”

Add the rising Russian challenge to the European order, which Mr. Vickers categorizes as “a fairly near-term problem,” along with “the things that could happen on the Korean Peninsula.”

And the over-the-horizon threats?

“When you step back a bit and look at enduring strategic problems,” he said, “then you look at the Middle East, where you have terrorism and proxy wars and the danger of religious wars and dangers of sectarian conflict.” He warns that religious and sectarian wars tend to be viciously heartfelt, and therefore bloody and protracted.

Attention must be paid to what, he predicts, will be this century’s most dynamic region: “East Asia and the rise of China — how to engage and manage that relationship and that with our allies, and keep the peace in that region.”

Each of those regions poses a difficult challenge for American policy makers, but Mr. Vickers warned of the prospect of more than one exploding simultaneously, with individual risks turning into a cascade of crises from, say, Mali to Pakistan or across East Asia.

“The challenge in the current world is that, for the first time since early in the Cold War, you have more of a risk of crises in multiple regions turning into broader conflict,” he said.

DURING the Cold War, Mr. Vickers was a member of the Green Berets assigned to infiltrate Warsaw Pact borders should World War III break out. His mission: Detonate a portable nuclear bomb to blunt an attack by the overwhelming numbers of Soviet tanks.

He was sent to Central America and the Caribbean during the era of small anticommunist wars, helping to end an airline hijacking and a hostage case involving Honduran government officials. He was also assigned to what a military biography euphemistically calls “contingency operations against the Sandinista regime in Nicaragua.”

Leaving the Army for the Central Intelligence Agency, he joined the invasion of Grenada. And after the Marine barracks in Beirut were bombed in 1983, killing 241 United States servicemen, he was given sensitive counterterrorism work in Lebanon.

As a rising C.I.A. officer, Mr. Vickers was the chief strategist for the largest covert action in American history, smuggling arms and money to Afghan mujahedeen battling Soviet invaders in Afghanistan.

After the collapse of communism in Europe, Mr. Vickers took a break in the policy world, writing white papers on budgets and strategy and how to restructure the military — until he was summoned to the Pentagon not long after the terrorist attacks on Sept. 11, 2001.

The grim connection was not lost on Mr. Vickers.

Al Qaeda blossomed among those same anti-Soviet “freedom fighters” in the years when Afghanistan, which had received billions of dollars in covert American assistance during the Soviet occupation, was paid scant attention by Washington after Moscow’s army marched home in disgrace.

“We made a mistake at the end of the Cold War by disengaging from that region,” Mr. Vickers said, “and I don’t think we want to do that again.”

FOR the past eight years at the Pentagon, he first managed Special Operations policy and then intelligence programs. He was former Defense Secretary Robert M. Gates’s handpicked liaison to the C.I.A. for the SEAL Team 6 mission that killed Osama bin Laden.

Mr. Vickers’s efforts contributed to the accelerated expansion of Special Operations forces — doubling personnel numbers, tripling their budget and quadrupling the pace of deployments.

But there is another military truism — if your favorite tool is a hammer, then every problem looks like a nail — and Mr. Vickers is aware of the dangers for the Special Operations forces.

“For all of the capabilities that S.O.F. has as a force-multiplier, as a small-footprint, big-impact force, it is not a panacea for all of your strategic problems,” he said.

Mr. Vickers’s Pentagon tour also witnessed growth in another signature weapon of the post-9/11 period: unmanned aerial vehicles for surveillance and attack. Early in the counterterrorism wars, the Pentagon could barely keep half a dozen drones airborne at one time; the ceiling now is 65.

“The combination of ‘armed,’ ‘precision,’ ‘reconnaissance’ has been one of the most dramatic innovations,” he said. “It has been a critical operational instrument in the successes we have had against core Al Qaeda, in particular.”

Yet the drone program has come under harsh public scrutiny, especially since President Obama revealed that a January strike by a C.I.A. drone on a Qaeda target in Pakistan killed two Western hostages, one of them an American. Mr. Vickers demurred when asked whether that portion of the lethal drone program now operated covertly by the C.I.A. should fold under the Pentagon.

But he addressed the broader issue of whether the benefits of killing terrorists with remotely piloted, pinpoint strikes by drones outweighs the risks of alienating the public.

“As precise as this instrument is, as important as this instrument is, it is one tool and it is not enough to bring stability to an area,” he said. Landing Hellfire missiles on terrorists does not end terrorism; policy has to address the underlying local grievances that lead to radicalism, he added.

To strategically defeat adversaries, he said, “you have to change the postwar governance to make the victory stick.”

With a résumé that reads like an action-movie character’s biography, Mr. Vickers has been depicted in one film, “Charlie Wilson’s War,” and drawn into controversy over another, “Zero Dark Thirty.” He was absolved after a two-year inquiry into whether classified information was leaked to the filmmakers behind “Zero Dark Thirty.” Critics had argued that administration officials hoped the movie could burnish the president’s commander-in-chief credibility.

Near the conclusion of his retirement ceremony on Thursday, Mr. Vickers said he already had a glimpse of his new, quieter life.

He said that when a Pentagon work crew removed a special telephone installed in his home for after-hours secure communications, he found that his cable connection was accidentally cut at the same time — and he had lost all access to the outside world via Internet and TV.